Vacation rentals in Deerfield

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Top-rated vacation rentals in Deerfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Apartment in Shelburne Falls
4.87 out of 5 average rating, 485 reviews

Sunny downtown 2BR, near Bridge of Flowers

Urban 3-room (2 bdrm) apartment on 3rd floor of funky older apt building on the main street of Shelburne Falls. Apartment faces the street, with views of the hills beyond. New kitchen appliances, and newly remodeled bath with custom shower, tile floor, and washer/dryer. Interesting art throughout the apartment, including some original pieces. Steps to the Glacial Potholes, Bridge of Flowers; and all the galleries, shops, restaurants, and cafes that this charming New England village has to offer.

Top guest favorite
A two-story building is shown, featuring a red exterior complemented by a wooden deck with railings. Stairs lead up to the deck entrance. A green vehicle is parked nearby, with trash and recycling bins on the side. Leafless trees provide a backdrop.
Apartment in Williamsburg
4.96 out of 5 average rating, 142 reviews

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Top guest favorite
A charming Greek Revival farmhouse features a covered porch adorned with ferns and surrounded by lush greenery. The exterior showcases dark shutters and light green siding, framed by trees that provide shade and tranquility.
Apartment in Conway
4.98 out of 5 average rating, 112 reviews

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the famed Tree House Brewery, just 10 min away. There are many sights, country roads, trails to explore, along with many varied restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Top guest favorite
The exterior of a charming studio is showcased, featuring a low stone façade and a modern art sculpture in front of the lush green lawn. Solar panels are visible on the roof, and colorful decor accents the windows.
Guest suite in Greenfield
4.95 out of 5 average rating, 223 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Top guest favorite
Apartment in Shelburne Falls
4.97 out of 5 average rating, 386 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, ​walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

Guest favorite
A well-lit guest suite features a queen-sized bed with quality linens, positioned against a wall. A cozy day bed offers additional sleeping space. A round table and chairs complement the room, while large windows allow natural light to fill the space. A patterned area rug adds warmth.
Guest suite in Montague
4.91 out of 5 average rating, 245 reviews

Great Falls Private Suite

Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon. We are between downtown Turners Falls and Greenfield. If you're looking for a private and bright suite with beautiful natural light and a modern bohemian feel this is the space for you! Please note that there is a kitchenette but not a full kitchen. Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the CT River.

Top guest favorite
Barn in Northampton
4.97 out of 5 average rating, 662 reviews

Brookside Carriage House. Private, Great Location.

1890's Carriage House. Bright 850 sq. ft., 2nd flr. studio. Original wood flrs, 12' ceiling, skylights, modern amenities w/ rustic charm. Onsite parking. Two sleeping nooks: One QUEEN, One FULL bed & a leather couch; open floor plan. Shower, laundry, full kitchen, dining table, lounging area, Juliet balconey. Eclectic, spacious, private, quiet, all in a fantastic location. This is a large studio. Staircase to 2nd floor. No TV. Dog friendly; contact me first. Non-Smoking/vaping.

Top guest favorite
Apartment in Greenfield
4.95 out of 5 average rating, 108 reviews

Cozy one bedroom apartment

This is a beautiful one bedroom apartment located on the first floor that was recently remodeled. The stylish place is perfect for 2 people. It has a good size kitchen and a porch in the back. Located on a quiet and safe street yet close local restaurants and coffee shops. Easy hikes with great views like Poet Seat Tower and Highland Park. Also close to Deerfield Academy, Northfield Mount Hermon, The Bement School, Eaglebrook Schoool and Stonleigh-Burnham School.

Top guest favorite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Apartment in Conway
4.96 out of 5 average rating, 209 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Top guest favorite
The exterior of the apartment is displayed, showcasing a light-colored siding with two dormer windows on the roof. A well-maintained lawn is visible, along with a white privacy fence surrounding the backyard area.
Apartment in Greenfield
4.96 out of 5 average rating, 474 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, safe neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

Top guest favorite
The entrance features a wooden staircase leading to a covered porch with decorative columns. A red door serves as the focal point, complemented by large windows on either side that allow natural light to illuminate the area. Lush plants line the path, enhancing the inviting entrance.
Apartment in Greenfield
4.98 out of 5 average rating, 228 reviews

Lovely 2nd floor Apartment

This lovely spacious 1 bedroom apartment is situated on a quiet street in the heart of Greenfield. Only a 3 minute ride to a charming downtown & restaurants Enjoy lots of natural light and a calm office space with an additional futon for rest. Free parking on premises and access to nearby baseball field and tennis courts. A place you'll love to come back to.

Top guest favorite
Apartment in South Deerfield
4.97 out of 5 average rating, 133 reviews

Guest house-rural setting with a fabulous view!

Located in South Deerfield, close to Amherst and Northampton. Private and secure entry to guest house. Fully equipped kitchen, dining area with living room, bedroom with queen bed. Enjoy your own quiet space with lots of privacy and mountain views. Perfect accommodations for 2 adults.

Popular amenities for Deerfield vacation rentals

When is the best time to visit Deerfield?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Deerfield?

    Deerfield has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Deerfield?

    Experience the best of Deerfield with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Deerfield?

    Yes! Work meets play with ease at over 10 vacation rentals in Deerfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Deerfield have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Deerfield have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Deerfield have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Deerfield have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Deerfield?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Deerfield

  • Total vacation rentals

    Explore 20 vacation rentals in Deerfield

  • Nightly prices starting at

    Deerfield vacation rentals start at € 94 per night before taxes and fees

  • Verified guest reviews

    Over 1,760 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Deerfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Deerfield rentals

  • 5 Average rating

    Deerfield stays are highly rated by guests—averaging 5 out of 5!